Can Stefanos Tsitsipas maintain his unbeaten record against Kevin Anderson as he faces off against the Wimbledon finalist in Shanghai?

World no. 8 Kevin Anderson is out to secure a place in the quarterfinals of the Shanghai Rolex Masters on Thursday, but he’ll have to do something he’s never done before – beat Toronto runner-up Stefanos Tsitsipas.

Kevin Anderson lost to Stefanos Tsitsipas in Toronto (Photo by Vaughn Ridley/Getty Images)

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Anderson is in seventh place on the Race to London and leads Dominic Thiem by only 15 points – but with Thiem already out of the Rolex Shanghai Masters at the hands of Matthew Ebden, the South African has the opportunity to widen the gap and boost his chances of qualifying for the season-ending championships by going deeper in Shanghai.

In eight previous appearances in Shanghai, Anderson has only made it as far as the quarterfinals once, doing so in 2015 when he beat Kei Nishikori before losing to Jo-Wilfried Tsonga. He was defeated in the second round on subsequent appearances by Gael Monfils and Jan-Lennard Struff respectively.

There were no such difficulties for Anderson, seeded seventh, when he opened his 2018 campaign against qualifier Mikhail Kukushkin. In a match that took just over an hour, Anderson struck 14 aces on his way to a 6-2, 6-4 win over Kukushkin.

Runner-up at the US Open in 2017 and Wimbledon in 2018, Anderson has played some of the best tennis of his career over the past 18 months and has had some of the best Masters 1000 Series results of his career, too. Before 2018, Anderson had made eight quarterfinals since 2009 and never gone beyond; in 2018, he made quarterfinals in Indian Wells and Miami and reached the semifinals of the Madrid Masters and the Canada Masters.

Defeated in the quarterfinals of Tokyo last week by Richard Gasquet in a pair of tie-breaks, Anderson has nevertheless already equaled the total number of matches he won after the US Open in 2017 – three – but with the prospect of qualifying for the Nitto ATP Finals for the very first time, he still has everything to play for in Shanghai, where he is on a potential quarterfinal collision course with Novak Djokovic.

First, though, he has to get past Stefanos Tsitsipas, who cost Anderson perhaps his best opportunity to reach a first Masters 1000 Series final in Toronto this summer.

Tsitsipas has already qualified for the Next Gen ATP Finals, the first player to do so if one doesn’t count Alexander Zverev, who will presumably be playing the Nitto ATP Finals. But Tsitsipas has his mind on bigger things:

Just got informed that I qualified for the @nextgenfinals in Milan this November. Can’t wait to see the exact same photo but for the @atpworldtour finals in London.

Currently in 12th place in the Race to London and trailing the player in eighth place, Dominic Thiem, by 1,710 points, Tsitsipas’s chances of qualifying for the season-ending championships look quite slim – but one has to commend his ambition, and the fact that he’s even in the conversation is impressive in its own right, given that he was ranked world no. 91 when he made the quarterfinals of the Doha 250 as a qualifier at the very beginning of the year.

Stefanos Tsitsipas (WANG ZHAO/AFP/Getty Images)

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Tsitsipas’s run to his first ATP World Tour final at the 500-level Barcelona Open in April, and his subsequent semifinal finish in Estoril, saw him break into the top 50 by the time the first six months of the year were done, even before he reached the round of 16 at Wimbledon. The Greek had already got two wins over top-10 players by the time he made the semifinals of the Citi Open in Washington, D.C. in August, but it was the run that followed at the Canada Masters which really got people talking as Tsitsipas beat Thiem, Novak Djokovic, Alexander Zverev and Anderson to achieve something which many much older, higher-ranked and more accomplished players (like Anderson) have never managed – reaching a Masters 1000 Series final.

Tsitsipas would only win one of his next four matches, but he had a good week last week in Tokyo where he beat Taro Daniel and Alex de Minaur to make the quarterfinals before losing to Kei Nishikori in a tight quarterfinal encounter, and he is obviously playing well in Shanghai: Not only did he beat Gael Monfils in an entertaining three-set first-round match, but backed it up with a very solid 6-4, 7-6(8) victory over rising Russian Karen Khachanov.

Both his previous matches with Anderson have gone the way of Tsitsipas, with the now-world no. 15 beating the South African on clay in Estoril in April and, more impressively, in the aforementioned Toronto semifinal clash, although that one was settled only be a third-set tie-break. One feels that the quick court in Shanghai should suit Anderson, although it’s not a terrible surface for Tsitsipas either, and indeed this match feels almost impossible to call. Whoever should come through to the quarterfinals at the Rolex Shanghai Masters and a likely clash with Djokovic, they are probably going to have had to win at least one tie-break to do so.